Adenine tautomers: Relative stabilities, ionization energies, and mismatch with cytosine

Journal of Physical Chemistry A

Volumn 110, Issue 11, 2006, Pages 4012-4020

  Fonseca Guerra, C ^a   Bickelhaupt, F M ^a   Sana, S ^b   Wang, F ^b  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b SWINBURNE UNIVERSITY OF TECHNOLOGY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; IONIZATION; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; PROBABILITY DENSITY FUNCTION;

ADENINE TAUTOMERS; KOHN-SHAM ORBITALS; ORBITAL ENERGIES; RADICAL CATIONS;

NITROGEN COMPOUNDS;

ADENINE; CYTOSINE; DRUG DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM;

ADENINE; CYTOSINE; ISOMERISM; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 33645657530     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp057275r     Document Type: Article

References (74)

1. (a) Watson, J. D.; Crick, F. H. C Nature (London) 1953,171, 964.
2. (b) Topal, M. D.; Fresco J. R. Nature (London) 1976, 263, 285.
3. (c) Harris, V. H.; Smith, C. L.; Cummins, W. J.; Hamilton, A. L.; Adams, H.; Dickman, M.; Hornby, D. P.; Williams, D. M. J. Mol. Biol. 2003, 326, 1389.
4. (a) Hanus, M.; Kabelác, M.; Rejnek, J.; Ryjácek, F.; Hobza, P. J. Phys. Chem. B 2004, 108, 2087.
5. (b) Gorb, L.; Podolyan, Y.; Leszczynski, J.; Siebrand, W.; Fernândez-Ramos, A.; Smedarchina, Z. Biopolymers 2002, 61, 77.
6. (c) Rueda, M.; Luque, F. J.; Lopez, J. M.; Orozco, M. J. Phys. Chem. A 2001,105, 6575,
7. (d) Blas, J. M.; Luque, F. J.; Orozco, M. J. Am. Chem. Soc. 2004, 126, 154.
8. (a) Danilov, V. I.; Anisimov, V. M.; Kurita, N.; Hovorun, D. Chem. Phys. Lett. 2005, 412, 285.
9. (b) Kawahara, S.-I.; Uchimaru, T.; Sekine, M. J. Mol. Struct. 2000, 530, 109.
10. (c) Zhanpeisov, N. U.; Sponer, J.; Leszczynski, J. J. Phys. Chem. A 1998, 102, 10374.
11. (a) Guckian, K. M.; Krugh, T. R.; Kool, E. T. J Am. Chem. Soc. 2000,122, 6841.
12. (b) Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem. 2000, 112, 1046.
13. (c) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 1001.
14. (a) Fonseca Guerra, C.; Bickelhaupt, F. M. Angew. Chem. 2002, 114, 2194;
15. Angew. Chem., Int. Ed. 2002,41, 2092.
16. (b) Fonseca Guerra, C.; Bickelhaupt, F. M. J. Chem. Phys. 2003, 119. 4262.
17. (a) Gupta, D.; Roitzsch, M.; Lippen, B. Chem. Eur. J. 2005, 11, 6643,
18. (b) Gupta, D.; Huelsekopf, M.; Morell Cerdà, M.; Ludwig, R.; Lippert, B. Inorg. Chem. 2004, 43, 3386.
19. (c) Miguel, P. J. S.; Lax, P.; Willermann, M.; Lippen, B. Inorg. Chim. Acta 2004, 357, 4552.
20. (d) Müller, J.; Sigel, R. K. O.; Lippert, B. J. Inorg. Biochem. 2000, 79, 261.
21. (e) Sponer, J.; Sponer, J. E.; Gorb, L.; Leszczynski, J.; Lippert, B. J. Phys. Chem. A 1999, 103, 11406.
22. (f) Zamora, F.; Kunsman, M.; Sabat, M.; Lippert, B. Inorg. hem. 1997, 36, 1583.
23. (a) Plützer, Chr.; Kleinermanns, K. Phys. Chem. Chem. Phys. 2002, 4, 4877.
24. (b) Plützer, Chr.; Nir, E.; de Vries, M. S.; Kleinermanns, K. Phys. Chem. Chem. Phys. 2001, 3, 5469.
25. (c) Marian, C.; Nolting, D.; Weinkauf, R. Phys. Chem. Chem. Phys. 2005, 7, 3306.
26. (d) Nir, E.; Plutzer, Chr.; Kleinermanns, K.; de Vries, M. Eur. Phys. J. D 2002, 20, 317.
27. (e) Chin, W.; Dimicoli, I.; Piuzzi, F.; Tardivel, B.; Elhanine, M. Eur. Phys. J. D 2002,20, 347.
28. (f) Mons, M.; Dimicoli, I.; Piuzzi, F.; Tardivel, B.; Elhanine, M. J. Phys. Chem. A 2002,106, 5088.
29. (g) Piuzzi, F.; Mons, M.; Dimicoli, I.; Tardivel, B.; Zhao, Q. Chem. Phys. 2001, 270, 205.
30. (a) Laxer, A.; Major, D. T.; Gottlieb, H. E.; Fisher, B. J. Org. Chem. 2001,66, 5463.
31. (b) Secárová, P.; Marek, R.; Malinákov K.; Kolehmainen, E.; Hocková, D.; Hocek, M.; Sklenár, V. Tetrahedron Lett. 2004, 45, 6259.
32. (a) Fonseca Guerra C.; Bickelhaupt, F. M. Angew. Chem. 1999, 111, 3120;
33. Angew. Chem., Int. Ed. 1999, 38, 2942.
34. (b) Fonseca Guerra, C.; Bickelhaupt, F. M.; Snijders J. G.; Baerends, E. J. J. Am. Chem. Soc. 2000, 122, 4117.
35. (a) Chong, D. P.; Gritsenko, O. V.; Baerends, E. J. J. Chem. Phys. 2002, 116, 1760.
36. (b) Gritsenko, O. V.; Braïda, B.; Baerends, E. J. J. Chem. Phys. 2003, 119, 1937.
37. (c) Lemierre, V.; Chrostowska, A.; Dargelos, A.; Chermette, H. J. Phys. Chem. A 2005, 109, 8348.
38. Bickelhaupt, F. M.; Baerends, E. J. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; Wiley-VCH; New York, 2000; Vol. 15, pp 1-86.
39. Fonseca Guerra, C.; Bickelhaupt, F. M.; Snijders, J. G.; Baerends, E. J. Chem. Eur. J. 1999, 5, 3581.
40. (a) te Velde, G.; Bickelhaupt, F. M.; van Gisbergen, S. J. A.; Fonseca Guerra, C.; Baerends, E. J.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931.
41. (b) Fonseca Guerra, C.; Visser, O.; Snijders, J. G.; te Velde, G.; Baerends, E. J. In Methods and Techniques for Computational Chemistry; Clementi, E., Corongiu, G., Eds.; STEF; Cagliari, 1995; pp 305-395.
42. (c) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
43. (d) Baerends, E. J.; Ros, P. Chem. Phys. 1975, 8, 412.
44. (e) Baerends, E. J.; Ros, P. Int. J. Quantum Chem. Symp. 1978, 12, 169.
45. (f) Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Theor. Chem. Ace. 1998, 99, 391.
46. (g) Boerrigter, P. M.; te Velde, G.; Baerends, E. J. Int. J. Quantum Chem. 1988, 33, 87.
47. (h) te Velde, G.; Baerends, E. J. J. Comput. Phys. 1992, 99, 84.
48. (i) Snijders, J. G.; Baerends, E. J.; Vemooijs, P. At. Nucl. Data Tables 1982, 26, 483.
49. (j) Krijn, J. Baerends, E. J. Fit-Functions in the HFS-Method; Internal Report (in Dutch); Vrije Universiteit; Amsterdam, 1984.
50. (k) Versluis, L.; Ziegler, T. J. Chem. Phys. 1988, 88, 322.
51. (l) Slater, J. C. Quantum Theory of Molecules and Solids; McGraw-Hill: New York, 1974; Vol. 4.
52. (m) Becke, A. D. J. Chem. Phys. 1986, 84, 4524.
53. (n) Becke, A. Phys. Rev. A 1988, 38, 3098.
54. (o) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
55. (p) Perdew, J. P. Phys. Rev. B 1986, 33, 8822 (Erratum; Phys. Rev. B 1986, 34, 7406).
56. (q) Fan, L.; Ziegler, T. J. Chem. Phys. 1991, 94, 6057.
57. (a) von Niessen, W.; Schirmer, J.; Cederbaum, L. S. Comput. Phys. Rep. 1984, 1, 57.
58. (b) Cederbaum, L. S.; Domcke, W. Adv. Chem. Phys. 1977, 36, 205.
59. (a) TZVP basis set; Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.
60. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
61. (a) Morokuma, K. Chem. Phys. 1971, 55, 1236.
62. (b) Kitaura, K.; Morokuma, K. Int. J, Quantum. Chem. 1976, 10, 325.
63. (a) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1755.
64. (b) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1558.
65. (c) Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977,46, 1.
66. (a) Stone, A. J. The Theory of Intermolecular Forces; Clarendon Press: Oxford, 1996.
67. (b) Stone, A. J. Chem. Phys. Lett. 1993, 211, 101.
68. Poater, J.; Sola, M.; Bickelhaupt, F. M. Chem. Eur. J. In press.
69. Preuss, M.; Schmidt, W. G.; Seino, K.; Furthmüller, J.; Bechstedt, F. J. Comput. Chem. 2004, 25, 112.
70. (a) Lin, J.; Yu, C.; Peng, S.; Akiyama, I.; Li, K.; Lee, L. K.; LeBreton, P. R. J. Am. Chem. Soc. 1980, 102, 4627.
71. (b) Orlov, V. M.; Smirnov, A. N.; Varshavsky, Y. M. Tetrahedron Lett. 1976, 17, 4377.
72. (a) Crespo-Hernandez, C. E.; Arce, R.; Ishikawa, Y.; Gorb, L.; Leszczynski, J.; Close D. M. J. Phys. Chem. A 2004, 108, 6373.
73. (b) Dolgounitcheva, O.; Zakrzewski, V. G.; Ortiz, J. V. Int. J. Quantum Chem. 2000, 80, 831.
74. Wang, F.; Downtown, M. T.; Kidwani, N. J. Theor. Comput. Chem. 2005, 4, 247.